3,4-Dibromothiophene → 3,4-Bis(trimethylsilylethynyl)thiophene

HRID 493445Notes

Reaction equation

HRID 493445 reaction equation
Br[C:2]1[C:6](Br)=[CH:5][S:4][CH:3]=1.[CH3:8][Si:9]([C:12]#[CH:13])([CH3:11])[CH3:10].O1[CH2:18][CH2:17]CC1.C(NC(C)C)(C)C>[Cu](I)I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:8][Si:9]([C:12]#[C:13][C:2]1[C:6]([C:17]#[C:18][Si:9]([CH3:11])([CH3:10])[CH3:8])=[CH:5][S:4][CH:3]=1)([CH3:11])[CH3:10]

Participants

6

Reactant 3

HCID 184523,4-DibromothiopheneHCID 66111TrimethylsilylacetyleneHCID 18968793THF diisopropylamine

Product 1

HCID 576816483,4-Bis(trimethylsilylethynyl)thiophene

Reagents, catalysts & solvents 2

HCID 11776TriphenylphosphineCatalystHCID 83717Copper iodideCatalyst

Conditions

Temperature
70 °C

Procedure

2.5 ml (22.6 mmol) of 3,4-dibromothiophene, commercially available from Aldrich under the Product No. 24, 715-4, and 8 ml (56.5 mmol) of trimethylsilylacetylene were mixed with a solvent of tetrahydrofuran/diisopropylamine (1:1), and 0.15 g (0.23 mmol) of palladium dichlorodiphosphine, 21 mg (0.11 mmol) of copper iodide and 0.1 g (0.36 mmol) of triphenylphosphine were then sequentially added thereto. The reaction solution was heated at 70° C. for 8 hours, and washed with an aqueous solution of ammonium chloride. The resulting organic layer was dried over magnesium sulfate, dried under reduced pressure, and purified using silica gel column chromatography, thus obtaining 1.5 g of 3,4-bis(trimethylsilylethynyl)thiophene (IIa).

Workup

  1. additionwere then sequentially added
  2. washwashed with an aqueous solution of ammonium chloride
  3. dry with materialThe resulting organic layer was dried over magnesium sulfate
  4. customdried under reduced pressure
  5. custompurified

Sources & evidence

ORD record
ord-92ab3581d50b4be2b032232b2d2cd629
Source dataset
uspto-grants-2009_05
Patent number
US07534899B2

Reaction notes

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